N-bromobutanimide → HCID 178478248, compound

HRID 1774709Notes

Reaction equation

HRID 1774709 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[Br:11]N1C(=O)CCC1=O>C(O)(=O)C>[Br:11][C:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[Cl:1])[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3100454-Chloro-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 178478248HCID 178478248, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-chloro-1H-pyrazolo[3,4-b]pyridine (6) 1 g (6.53 mmoles) in acetic acid (100 mL) cooled to 0° C. was added N-bromosuccinimide 2.31 g (13.06 mmol and the resulting RM was stirred for 4 hr at rt. After completion of the SM, the RM was quenched with ice water and extracted with dichlromethane (2×10 mL). The combined organic layer was dried over sodium sulphate, and the solvent evaporated to yield compound 7 (Yield: 0.9 g, 60%). 1H NMR (400 MHz, CDCl3): δ 13.19 (br s, 1H), 8.21 (s, 1H), 7.39 (m, 1H).

Workup

  1. customAfter completion of the SM, the RM was quenched with ice water
  2. extractionextracted with dichlromethane (2×10 mL)
  3. dry with materialThe combined organic layer was dried over sodium sulphate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-c1c22a829d66449d9b5948e93f985654
Source dataset
uspto-grants-2016_02
Patent number
US09260426B2

Reaction notes

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